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Dating Diaries: Chris and Stacey

Stacey leaned in and said that she wanted to kiss Chris. But he felt a little uncomfortable with everyone around.

Stacey showed up, on time, I was like, wow. She was smoking hot. (dreamstime photo illustration)

By Special to the Star

Sat., Dec. 3, 2016

Chris is a 31-year-old “former corporate-slave senior manager turned sales professional for a start-up” who lives in Leaside. He says “I’m slightly trendier than your average guy, but too cheap to shop anything high end.” Chris says he would be described as “personable, articulate, charismatic, open-minded, patient, funny and authentic. I like to tell stories; I love going out and being the centre of attention; I am who I am, whether it’s online or off.” Chris likes to travel and eat food from different cultures. He says “I suffer from ‘analysis paralysis.’ I need to take more risks in life, and live in the moment.”

I’ve been single for eight years, most of that by choice. The first and only relationship I’ve been in lasted less than a year. We met online, but also attended the same university. She cheated on me, and I had a hard time trusting people after that. The idea of meeting someone online stuck with me, so I joined a plethora of sites. The online world is cruel towards shorter men, and men who are visible minorities, like me.

Dating apps mean women judge you on less. I decided to go on as many dates as I could, to prove to myself I was “datable.” Since then I’ve become a bit more serious about finding “the one.” I’m looking for a woman who is emotionally available, communicative, responsible with money, into travel, and has an inner child. There’s nothing more boring than a woman who can’t make light of things.

I met Stacey through a dating app. I had just come back from travelling in Asia, and she had just come back from working abroad for a few years, which I thought was cool. We were both in career transitions, the same life stage.

The texting chemistry wasn’t that great. We set a date for a Friday but that night we were both tired, so we moved it to Saturday, but that night we were both out with friends, so we pushed it later a few times, and then we were both too tired, so we agreed to meet on the Sunday afternoon. I appreciated that we both tried to find a good time, instead of just the guy doing it.

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We went to a pub on King West. We hadn’t talked much before the date so I wasn’t sure what to expect. I wasn’t looking forward to it — it was just another date for me. But when Stacey showed up, on time, I was like, wow. She was smoking hot. We greeted each other with hugs.

We shared a bottle of wine. I don’t usually drink that much. I had to know more about her time abroad, so I asked her a lot of questions. I learned a lot about her interests and influences. As we drank more, I moved closer towards her. Our legs grazed under the table. The conversation wasn’t sexual in nature, it was very lighthearted and fun, but the sexual chemistry was building.

We grabbed the bill and went for a stroll, ending up on Queen West. Stacey told me that she wanted to get another drink. At the next bar, as we were sitting across from each other, she leaned in and said that she wanted to kiss me. Yaaas! But I felt a little uncomfortable with everyone around. I probably should have just kissed her then. We left, and outside I laid one on her as we started walking again. She invited me back to her place.

I could see where this was going. It’s not where I intended it to go at all. It was night when we got back to her place. We sat on the couch and we started kissing. Basically, you know what happens next. It wasn’t the best performance from either of us, which I blame on exhaustion.

I tried to see Stacey again after that. She told me over text that she wanted to get together for drinks, and admitted that she was just out of a long relationship and hadn’t told me, and isn’t ready for anything other than fun dates. She said that she had a lot of fun with me, though. Not knowing exactly what “fun dates” meant, I told her this was also exactly what I’m into at the moment. I proposed to her a fun date of a games night. She wasn’t into it.

After that, she disappeared. I saw her on the app again recently. We didn’t connect again.

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